Water → 4-Bromo-1,5-dimethyl-1H-pyrrole-2-carbonitrile

HRID 515896Notes

Reaction equation

HRID 515896 reaction equation
[Br:1]Br.[CH3:3][N:4]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]1[C:10]#[N:11].O>C(O)(=O)C>[Br:1][C:7]1[CH:6]=[C:5]([C:10]#[N:11])[N:4]([CH3:3])[C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 918121,5-Dimethylpyrrole-2-carbonitrile

Product 1

HCID 153965834-Bromo-1,5-dimethyl-1H-pyrrole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (6.58 mL, 0.13 mol) in acetic acid (60 mL) is added dropwise, with the aid of a dropping funnel, to a solution of 1,5-dimethyl-1H-pyrrole-2-carbonitrile (15.0 g, 0.12 mol) in acetic acid (300 mL). The batch is stirred at ambient temperature for 24 hours. The reaction mixture is then poured into a beaker containing 300 mL of water. The solid formed is filtered off and rinsed with water. It is then dissolved in dichloromethane (300 mL) and the organic phase is washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to yield the expected product in the form of a solid.

Workup

  1. additionThe reaction mixture is then poured into a beaker
  2. customThe solid formed
  3. filtrationis filtered off
  4. washrinsed with water
  5. dissolutionIt is then dissolved in dichloromethane (300 mL)
  6. washthe organic phase is washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60861ae02ce44e1fbe727dd039bff5c6
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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